Skip to main content

Advertisement

Log in

An Experimental Study to Synthesize and Characterize Host–Guest Encapsulation of Anthracene, and the Quenching Effects of Co and Ni

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

A complex of anthracene with methyl-beta-cyclodextrin (A-Me-β-CD) having fluorophoric characteristics was obtained in aqueous medium. Spectroscopic and thermal analyses of the complex were performed by Fourier transform infrared spectroscopy and differential scanning calorimetry-thermogravimetry. The interaction of Me-β-CD and anthracene was also analyzed by means of spectrometry by a UV–Vis spectrophotometer. The stoichiometry of the complex was determined by the Benesi–Hildebrand method. The complex formation constant was found to be (42 ± 3) × 103 L·mol−1. The Gibbs energy and excited singlet state energy were calculated. The mechanism of the quenching effect of Co(II) and Ni(II) metals in the inclusion complex was studied. The Stern–Volmer constant, bimolecular quenching rate constant, lifetime and approximate activation energy values were determined, and the quenching was found to be diffusion controlled dynamic quenching. In addition, with the energy band calculations made, it was shown by means of Taug curves that electron transfer was made to Ni and Co metals from the complex fluorophore group in the quenching mechanism.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Anitha, A., Murugan, M., Rajamohan, R.: Molecular encapsulation of amodiaquine in 2-hydroxypropyl β-cyclodextrin cavity. Characterization and its in vitro cytotoxicity. Spectrosc. Lett. 51, 198–204 (2018)

    Article  CAS  Google Scholar 

  2. Murugan, M., Anitha, A., Sivakumar, K., Rajamohan, R.: Supramolecular ınteraction of primaquine with native β-cyclodextrin. J. Solution Chem. 47, 906–929 (2018)

    Article  CAS  Google Scholar 

  3. Sabari, C.L., Sivakumar, K., Rajamohan, R.: Improvement of cytotoxic activity of local anesthetics against human breast cancer cell line through the cyclodextrin complexes. J. Macromol. Sci. A 54, 402–410 (2017)

    Article  CAS  Google Scholar 

  4. Sambasevam, K.P., Mohamad, S., Sarih, N.M., Ismail, N.A.: Synthesis and characterization of the ınclusion complex of β-cyclodextrin and azomethine. Int. J. Mol. Sci. 14, 3671–3682 (2013)

    Article  CAS  Google Scholar 

  5. Norkus, E.: Metal ion complexes with native cyclodextrins. An overview. J. Incl. Phenom. Macrocycl. Chem. 65, 237–248 (2009)

    Article  CAS  Google Scholar 

  6. Kemtong, C., Banerjee, D., Liu, Y., El Khoury, J.M., Rinaldi, P.L., Hu, J.: Formation of an ınclusion complex of a new transition metal ligand in β-cyclodextrin. Supramol. Chem. 17, 335–341 (2005)

    Article  Google Scholar 

  7. Jullian, C., Brossard, V., Gonzalez, I., Alfaro, M., Olea-Azar, C.: Cyclodextrins-kaempferol ınclusion complexes: spectroscopic and reactivity studies. J. Solution Chem. 40, 727–739 (2011)

    Article  CAS  Google Scholar 

  8. Ay, U., Dogruyol, Z., Arsu, N.: The effect of heavy metals on the anthracene-me-β-cyclodextrin host-guest ınclusion complexes. Supramol. Chem. 26, 66–70 (2014)

    Article  CAS  Google Scholar 

  9. Ay, U., Sarlı, S.E.: Investigation by fluorescence technique of the quenching effect of Co2+ and Mn2+ transition metals, on naphthalene-methyl-beta-cyclodextrin host-guest ınclusion complex. J. Fluoresc. 28, 1371–1378 (2018)

    Article  CAS  Google Scholar 

  10. Morris, J.V., Mahoney, M.A., Huber, J.R.: Fluorescence quantum yield determinations. 9,10-dipenylanthracene as a reference standard in different solvents. J. Phys. Chem. 80, 969–974 (1976)

    Article  CAS  Google Scholar 

  11. Balta, D.K., Temel, G., Aydın, M., Arsu, N.: Thioxanthone based water-soluble photoinitiators for acrylamide photopolymerization. Eur. Polym. J. 46, 1374–1379 (2010)

    Article  CAS  Google Scholar 

  12. Ozkazanc, E., Ozkazanc, H., Gundogdu, O.: Characterization and charge transport mechanism of multifunctional polyfuran/tin(IV) oxide composite. J. Inorg. Organomet. 28, 2108–2120 (2018)

    Article  CAS  Google Scholar 

  13. Kumar, A., Kumar, A., Sharma, G., Al-Muhtaseb, A.H., Naushad, M., Ghfar, A.A., Stadler, F.J.: Quaternary magnetic BiOCl/g-C3N4/Cu2O/Fe3O4 nano-junction for visible light and solar powered degradation of sulfamethoxazole from aqueous environment. Chem. Eng. J. 334, 462–478 (2018)

    Article  CAS  Google Scholar 

  14. University of Zurich, Department of Chemistry Home Page. https://www.chem.uzh.ch/de/study/download/year2/che211.html

  15. Baggott, J.E., Pilling, M.J.: Temperature dependence of excited-state electron-transfer reactions quenching of RuL32+ emission by copper(II) and europium(III) in aqueous solution. J. Phys. Chem. 84, 3012–3019 (1980)

    Article  CAS  Google Scholar 

  16. Stanculescu, I., Dobrica, I., Mandravel, C., Mindrila, G.: Anal. Univ. Bucuresti-Chimie (serienoua) 19, 47 (2010)

    CAS  Google Scholar 

  17. Drössler, P., Holzer, W., Penzkofer, A., Hegemann, P.: Fluoresence quenching of riboflavin in aqueous solution by methionin and cystein. Chem. Phys. 286, 409–420 (2003)

    Article  Google Scholar 

  18. Marzouqi, A.H.A., Shehatta, I., Jobe, B., Dowaidar, A.: Phase solubility and inclusion complex of Itraconazole with ß-cyclodextrin using supercritical carbon dioxide. J. Pharm. Sci. 95, 292–304 (2006)

    Article  Google Scholar 

  19. Jadhav, G.S., Vavia, P.R.: Physicochemical, in silico and in vivo evaluation of a Danazol–β-cyclodextrin complex. Int. J. Pharm. 352, 5–16 (2008)

    Article  CAS  Google Scholar 

  20. Chow, D.D., Karara, A.K.: Characterization, dissolution and bioavailabilty in rats of Ibuprofen- β-cyclodextrin complex system. Int. J. Pharm. 28, 95–101 (1986)

    Article  CAS  Google Scholar 

  21. Uekama, K., Fujinaga, T., Otagiri, M., Hirayama, F., Yamasaki, M.: Inclusion complexations of steroid hormones with cyclodextrins in water and in solid phase. Int. J. Pharm. 10, 1–15 (1982)

    Article  CAS  Google Scholar 

  22. Rajagopalan, N., Chen, S.C., Chow, W.S.: A study of the inclusion complex of Amphotericin-B with γ-cyclodextrin. Int. J. Pharm. 29, 161–168 (1986)

    Article  CAS  Google Scholar 

  23. Uekama, K., Narisawa, S., Hirayama, F., Otagiri, A.: Improvement of dissolution and absorption characteristics of benzodiazepines by cyclodextrin complexation. Int. J. Pharm. 16, 327–338 (1983)

    Article  CAS  Google Scholar 

  24. Smulevich, G., Feis, A., Mazzi, G., Vincieri, F.F.: Inclusion complex formation of 1,8-dihydroxyanthraquinone with cyclodextrins in aqueous solution and in solid state. J. Pharm. Sci. 77, 523–526 (1988)

    Article  CAS  Google Scholar 

  25. Xiang, T.X., Andersoon, B.D.: Inclusion complexes of purine nucleosides with cyclodextrins: II. Investigation of inclusion complex geometry and cavity microenvironment. Int. J. Pharm. 59, 45–55 (1990)

    Article  CAS  Google Scholar 

  26. Singh, R., Bharti, N., Madan, J., Hiremath, S.N.: Characterization of cyclodextrin ınclusion complexes: a review. J. Pharm. Sci. Technol. 2, 171–183 (2010)

    CAS  Google Scholar 

  27. Ye, C.P., Ding, X.X., Li, W.Y., Mu, H., Wang, W., Feng, J.: Determination of crystalline thermodynamics and behavior of anthracene in different solvents. AIChE J. 64, 2160–2167 (2018)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We would like to thank the Kocaeli University Scientific Research Coordinator (BAP) (Project No: 2017/010), who contributed to the authors in this study, and the Gebze Technical University, Department of Chemistry, who helped to read the fluorescence lifetimes.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Umit Ay.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 80 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sarlı, S.E., Ay, U. An Experimental Study to Synthesize and Characterize Host–Guest Encapsulation of Anthracene, and the Quenching Effects of Co and Ni. J Solution Chem 48, 1535–1546 (2019). https://doi.org/10.1007/s10953-019-00932-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-019-00932-9

Keywords

Navigation